Chloroacetyl chloride → 2-Chloro-N-(2,6-dimethylphenyl)acetamide

HRID 2058850Notes

Reaction equation

HRID 2058850 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH2:4].C(N(CC)CC)C.[Cl:17][CH2:18][C:19](Cl)=[O:20]>C(Cl)Cl>[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:3]=1[NH:4][C:19](=[O:20])[CH2:18][Cl:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 68962,6-DimethylanilineHCID 8471Triethylamine

Product 1

HCID 707982-Chloro-N-(2,6-dimethylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 3-necked, 1-liter flask provided with a reflux condenser, an additional funnel and a magnetic stirring bar was charged 36.3 grams (0.3 mole) of 2,6-dimethyl aniline and 30.36 grams (0.3 mole) of triethylamine in 550 milliliters of methylene chloride. To the stirred solution, maintained at 0° to 5° C. by means of an ice bath, was added dropwise, over a period of 30 minutes, 33.9 grams (0.3 mole) of chloroacetyl chloride. The reaction mixture was then stirred at ambient temperature for 21 hours after which it was transferred to a separatory funnel and washed consecutively with 300 milliliter portions of 1 Normal hydrochloride acid, 10 percent aqueous sodium carbonate solution and water. The organic layer was removed, dried over magnesium sulfate and concentrated on a rotary evaporator at 55° C. leaving a bluish-gray solid. This solid was recrystallized from a hot 20:80 volume/volume ethylacetate-ligroin solution yielding 41 grams of gray, solid N-(2,6-dimethylphenyl)-α-chloroacetamide.

Workup

  1. customTo a 3-necked, 1-liter flask provided with a reflux condenser, an additional funnel and a magnetic stirring bar
  2. temperatureTo the stirred solution, maintained at 0° to 5° C. by means of an ice bath
  3. additionwas added dropwise, over a period of 30 minutes
  4. customwas transferred to a separatory funnel
  5. washwashed consecutively with 300 milliliter portions of 1 Normal hydrochloride acid, 10 percent aqueous sodium carbonate solution and water
  6. customThe organic layer was removed
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated on a rotary evaporator at 55° C.
  9. customleaving a bluish-gray solid
  10. customThis solid was recrystallized from a hot 20:80 volume/volume ethylacetate-ligroin solution

Sources & evidence

ORD record
ord-b63e6ad931c24a9e8ccd3d89495a5c64
Source dataset
uspto-grants-1982_03
Patent number
US04319917

Reaction notes

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